Asymmetric hetero-Diels-Alder reactions: X-ray structures of three novel chiral dihydropyrimidines

Elliott, Mark Christopher ORCID: https://orcid.org/0000-0003-0132-0818, Hibbs, David E., Hughes, D. S., Hursthouse, M. B., Kruiswijk, Elbertus and Malik, Khalifa M. Abdul 1998. Asymmetric hetero-Diels-Alder reactions: X-ray structures of three novel chiral dihydropyrimidines. Journal of Chemical Crystallography 28 (9) , pp. 663-671. 10.1023/A:1021791832534

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Abstract

Three novel dihydropyrimidine compounds N8,6-di(4-nitrophenyl)-(3R)-ethyl-(7R)-methyl-5-oxo-2,3,6,7-tetrahydrooxazolo[3,2,c] pyrimidine-8-carboxamide (2), N8,6-di((4-methylphenyl)-sulfonyl)-(3R)-ethyl-5-oxo-(7R)-phenyl-2,3,6,7-tetrahydrooxazolo [3,2,c]pyrimidine-8-carboxamide (3) and N8,6-di ((4-methylphenyl)sulfonyl)-(3R)-ethyl-(7R)-methyl-5-oxo-2,3,6,7-tetrahydrooxazolo[3,2,c] pyrimidine-8-carboxamide (4) have been prepared (from 2-amino-1-butanol of 64.4% e.e.) and structurally characterized by X-ray crystallography. All three compounds contain stereogenic centers, but the crystal of (2) chosen was found to be racemic whilst those of (3) and (4) were found to be homochiral. Compound (2) crystallizes in the monoclinic space group P21/c, with a = 17.958(4), b = 12.431(2), c = 9.653(2) Å, beta = 96.20(3)°, U = 2142.3(7) Å3, Z = 4, and D c = 1.449 g cm–3. Compounds (3) and (4) both crystallize in the monoclinic space group P21, with a = 9.349(2), b = 5.824(5), c = 26.513(8) Å, beta = 99.43(2)°, U = 1424.1(13) Å3, Z = 2 and D c = 1.389 g cm–3 for (3), and a = 5.9526(9), b = 16.3521(10), c = 13.2263(11) Å, beta = 92.81(12)°, U = 1285.9(2) Å3, Z = 2 and D c = 1.378 g cm–3 for (4).

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Chemistry
Subjects:	Q Science > QD Chemistry
Uncontrolled Keywords:	Pyrimidine - carboxamide - sulfonyl - chiral - crystal structure
Publisher:	Springer
ISSN:	1074-1542
Last Modified:	21 Oct 2022 10:22
URI:	https://orca.cardiff.ac.uk/id/eprint/39998

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